So I have a statue I modeled that I want to "break".  It's sort of a tall pillar, and I'd like to have it seem like it's broken in half but I don't think I have the skill to model the break itself and would rather be able to use a boolean operation to do so or something else.  Anyone have any ideas?

Whenever I need this, I use a boolean with a terrain. I cut a piece from the object I want to break by subtracting a terrain out of it. It looks very good.

By the way, I'd suggest to either use a procedural terrain or a standard terrain with a fairly high resolution, otherwise the polygons would show in the broken part and that's not nice.

I read your text better now and it seems you have to have your statue broken in two. Is this right? Sort of like what I did to the moon here?
http://www.renderosity.com/mod/gallery/index.php?image_id=1809042

If this is the case, you can do like this:
1- duplicate your object and duplicate your terrain, so that you have two exactly equal sets, exactly overlapping in space.
2- In one of the pairs statue+terrain, do a subtraction.
3- In the other pair statue+terrain, do an intersection.
4- Separate the two pairs from one another and you have a convincing broken object.

Depending on the context and the distance, it would be even more realistic if the two parts of the pillars dont match absolutely exactly, some missing pieces in one or both halves are to be expected. Easy enough to extend the suggested procedure to subtract another small terrain or two from the half pillars.

Do you guys ever encounter pieces left over?  I've been doing booleans with rocks and it looks great, but there's always left over little pieces hanging in mid air....any suggestions?

Those are artifacts of the operation, I think. Just bake the result of the operation and the pieces should disappear.
(remember to save a copy of the unbaked object, in case you want to adjust something later)

I dont think it should happen, and I cant say I remember it happening to me, but if worse come to worse you can try eliminating the extra bits by enclosing them in a primitive object and doing a bollean subtract, or enclosing the bit you want to keep in a primitive object and doing a boolean intersection.

I tried baking it but there was no change.....will try the terrain....